[name_m]Oakley[/name_m], [name_m]Oaks[/name_m], and Oakah ~ my favourite for you is [name_m]Oakley[/name_m], I just think it has a friendlier sound than the others somehow and feels ‘namier’ (although can see that Oakah would appeal if you’re a [name_m]Judah[/name_m] fan). [name_m]Oakley[/name_m] nn [name_m]Oaks[/name_m] goes so well with E!
[name_m]Theodore[/name_m] ~ I like him in the middle for you
[name_m]Rowan[/name_m] ~ I adore him and see what you mean about the similar letters across all your names, but he sounds SO cohesive/similar with E, how would you ever name another? 
[name_m]Augustine[/name_m] ~ love the meaningful date for you, but he just feels a bit much compared to most of your gentle, nature-y names. I think [name_m]August[/name_m] would be a nice nod to the symbolism but keeping the vibe of your other choices.
[name_m]Shepherd[/name_m], [name_f]Shiloh[/name_f], [name_m]Solomon[/name_m], and [name_m]Silas[/name_m] ~ I do think [name_m]Shepherd[/name_m] would be my pick for you (Wynnie and Shep?! Too sweet). Second I’d actually go [name_m]Silas[/name_m], with his cosy woodland vibes. I’m less a fan of [name_f]Shiloh[/name_f] than most berries I think, he does have a lovely soft gentle sound though. [name_m]Solomon[/name_m] feels a bit serious for your set.
[name_m]Judah[/name_m], [name_m]Jude[/name_m] (and [name_m]Wilder[/name_m]) ~ prefer [name_m]Jude[/name_m], he’s such a great middle and pairs very well with E’s middle. [name_m]Judah[/name_m] [name_m]Wilder[/name_m] sounds a bit choppy in my accent without the rounded -r sound (‘jud-uh wild-uh’). I do, however, love [name_m]Wilder[/name_m] for you - that connection to [name_f]Laura[/name_f] Ingalls [name_m]Wilder[/name_m] is, well, wild!
[name_m]Herschel[/name_m] ~ don’t dislike him at all but he feels a bit more clunky-old-man-vintage than the rest of your list.
[name_m]Earnest[/name_m] ~ …is also old man vintage, but the wordiness of him feels more you! [name_m]Earnest[/name_m] [name_m]Jude[/name_m] is perfect (‘sincere praise’!)